16733-97-4 → HCID 15411269, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3.7 g (50 mmol) of lithium cyclopentadienylide in 90 ml of anhydrous tetrahydrofuran is added to a solution of 11.1 g (40 mmol) of 4-fluoro-4'-methylsulfonylbenzophenone, prepared in Example 2, in 70 ml of anhydrous tetrahydrofuran, cooled to 10° C. The reaction medium is stirred for 2 hours at this temperature and then for 24 hours at room temperature. It is subsequently poured onto ice. After dilution with water, the mixture is extracted with t-butyl methyl ether. The organic phase is dried over magnesium sulfate and then concentrated in the cold. The residue obtained is chromatographed on silica gel in dichloromethane. The resulting oil crystallizes from a petroleum ether/t-butyl methyl ether mixture to give 3.6 g of 4-[(cyclopenta-2,4-dienylidene)(4-fluorophenyl)methyl]methylsulfonylbenzene in the form of orange crystals melting at 110° C.

Provenance & Evidence